Amino acid-based fluorescent chiral ionic liquid for enantiomeric recognition

Analytical Chemistry

Volumn 82, Issue 12, 2010, Pages 5028-5037

  Bwambok, David K ^a   Challa, Santhosh K ^a   Lowry, Mark ^a   Warner, Isiah M ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION PROPERTY; ANALYTES; CHIRAL IONIC LIQUIDS; CHIRAL SELECTOR; EMISSION BANDS; EMISSION WAVELENGTH; ENANTIOMERIC COMPOSITION; ETHYL ESTERS; EXCIMER EMISSIONS; EXCITATION EMISSION MATRICES; EXCITATION WAVELENGTH; FLUORESCENCE INTENSITIES; FLUORESCENCE PROPERTIES; FLUORESCENT REPORTER; IDEAL SYSTEMS; L-PHENYLALANINE; LONG-WAVELENGTH EMISSIONS; MULTIPLE ANALYTES; MULTIPLE EXCITATIONS; NON-FLUORESCENT COMPOUNDS; ROOM TEMPERATURE; SPECTRAL REGION; SYNTHESIS AND CHARACTERIZATION; THERMAL DECOMPOSITIONS; TRIFLUOROMETHANE;

ABSORPTION; AMINO ACIDS; CHIRALITY; CHLORINE COMPOUNDS; ENANTIOMERS; ENANTIOSELECTIVITY; ESTERIFICATION; ESTERS; GLUCOSE; IONIC LIQUIDS; IONIZATION OF LIQUIDS; LITHIUM; ORGANIC ACIDS; PYROLYSIS; SUGAR (SUCROSE); SULFUR COMPOUNDS;

FLUORESCENCE;

DRUG DERIVATIVE; FLUORESCENT DYE; IONIC LIQUID; L PHENYLALANINE ETHYLESTER; L-PHENYLALANINE ETHYLESTER; MONOSACCHARIDE; PHENYLALANINE; SOLVENT;

ARTICLE; CHEMISTRY; METHODOLOGY; SPECTROFLUOROMETRY; STEREOISOMERISM; SYNTHESIS; ANALOGS AND DERIVATIVES; PROCEDURES;

FLUORESCENT DYES; IONIC LIQUIDS; MONOSACCHARIDES; PHENYLALANINE; SOLVENTS; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM;

EID: 77953582674     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac9027774     Document Type: Article

References (72)

1. Islam, M. R., Mahdi, J. G., and Bowen, I. D. Drug Saf. 1997, 17, 149-165
2. Agranat, I., Caner, H., and Caldwell, A. Nat. Rev. Drug Discovery 2002, 1, 753-768
3. Caner, H., Groner, E., Levy, L., and Agranat, I. Drug Discovery Today 2004, 9, 105-110
4. FDAs Policy Statement for the Development of New Stereoisomeric Drugs; FED REGISTER, 1992. http://www.fda.gov/cder/guidance/stereo.htm.
5. Agrawal, Y. K., Bhatt, H. G., Raval, H. G., Oza, P. M., and Gogoi, P. J. Mini-Rev. Med. Chem. 2007, 7, 451-460
6. Kano, K. J. Phys. Org. Chem. 1997, 10, 286-291
7. Fanali, S. J. Chromatogr. A 2000, 875, 89-122
8. Fillet, M., Hubert, P., and Crommen, J. J. Chromatogr. A 2000, 875, 123-134
9. Chankvetadze, B. Chem. Soc. Rev. 2004, 33, 337-347
10. Dodziuk, H., Kozminski, W., and Ejchart, A. Chirality 2004, 16, 90-105
11. Juvancz, Z., Kendrovics, R. B., Ivanyi, R., and Szente, L. Electrophoresis 2008, 29, 1701-1712
12. Fakayode, S. O., Brady, P. N., Pollard, D. A., Mohammed, A. K., and Warner, I. M. Anal. Bioanal. Chem. 2009, 394, 1645-1653
13. Got, P. A. and Scherrmann, J. M. Pharm. Res. 1997, 14, 1516-1523
14. Hofstetter, H., Cary, J. R., Eleniste, P. P., Hertweck, J. K., Lindstrom, H. J., Ranieri, D. I., Smith, G. B., Undesser, L. P., Zeleke, J. M., Zeleke, T. K., and Hofstetter, O. Chirality 2005, 17, S9-S18
15. Hofstetter, H. and Hofstetter, O. TrAC, Trends Anal. Chem. 2005, 24, 869-879
16. Ward, T. J. and Farris, A. B. J. Chromatogr. A 2001, 906, 73-89
17. Ilisz, I., Berkecz, R., and Peter, A. J. Sep. Sci. 2006, 29, 1305-1321
18. Shamsi, S. A., Palmer, C. P., and Warner, I. M. Anal. Chem. 2001, 73, 140A-149A
19. Fakayode, S. O., Williams, A. A., Busch, M. A., Busch, K. W., and Warner, I. M. J. Fluoresc. 2006, 16, 659-670
20. Williams, A. A., Fakayode, S. O., Alpturk, O., Jones, C. M., Lowry, M., Strongin, R. M., and Warner, I. M. J. Fluoresc. 2008, 18, 285-296
21. Willlams, A. A., Fakayode, S. O., Lowry, M., and Warner, I. M. Chirality 2009, 21, 305-315
22. Okamoto, Y. and Yashima, E. Angew. Chem., Int. Ed. 1998, 37, 1020-1043
23. Tachibana, K. and Ohnishi, A. J. Chromatogr. A 2001, 906, 127-154
24. Yashima, E. J. Chromatogr. A 2001, 906, 105-125
25. Stringham, R. W. In Advances in Chromatography; CRC PRESS-TAYLOR & FRANCIS GROUP: Boca Raton, 2006; Vol. 44, pp 257 - 290.
26. Ali, I. and Aboul-Enein, H. Y. Curr. Pharm. Anal. 2007, 3, 71-82
27. Kuhn, R. Electrophoresis 1999, 20, 2605-2613
28. Hyun, M. H. Bull. Korean Chem. Soc. 2005, 26, 1153-1163
29. Tran, C. D., Oliveira, D., and Yu, S. F. Anal. Chem. 2006, 78, 1349-1356
30. Tran, C. D. and Oliveira, D. Anal. Biochem. 2006, 356, 51-58
31. Tran, C. D. Anal. Lett. 2007, 40, 2447-2464
32. Bwambok, D. K., Marwani, H. M., Fernand, V. E., Fakayode, S. O., Lowry, M., Negulescu, I., Strongin, R. M., and Warner, I. M. Chirality 2008, 20, 151-158
33. Anderson, J. L., Ding, J., Welton, T., and Armstrong, D. W. J. Am. Chem. Soc. 2002, 124, 14247-14254
34. Ding, J., Welton, T., and Armstrong, D. W. Anal. Chem. 2004, 76, 6819-6822
35. Yuan, L. M., Han, Y., Zhou, Y., Meng, X., Li, Z. Y., Zi, M., and Chang, Y. X. Anal. Lett. 2006, 39, 1439-1449
36. Baker, G. A., Baker, S. N., Pandey, S., and Bright, F. V. Analyst 2005, 130, 800-808
37. Anderson, J. L., Armstrong, D. W., and Wei, G. T. Anal. Chem. 2006, 78, 2892-2902
38. Soukup-Hein, R. J., Warnke, M. M., and Armstrong, D. W. Ann. Rev. Anal. Chem. 2009, 2, 145-168
39. Han, X. and Armstrong, D. W. Acc. Chem. Res. 2007, 40, 1079-1086
40. Stalcup, A. M. and Cabovska, B. J. Liq. Chromatogr. Relat. Technol. 2004, 27, 1443-1459
41. Shamsi, S. A. and Danielson, N. D. J. Sep. Sci. 2007, 30, 1729-1750
42. Polyakova, Y., Koo, Y. M., and Row, K. H. Rev. Anal. Chem. 2007, 26, 77-98
43. Welton, T. Chem. Rev. 1999, 99, 2071-2083
44. Smiglak, M., Metlen, A., and Rogers, R. D. Acc. Chem. Res. 2007, 40, 1182-1192
45. Yu, S. F., Lindeman, S., and Tran, C. D. J. Org. Chem. 2008, 73, 2576-2591
46. Bica, K. and Gaertner, P. Eur. J. Org. Chem. 2008, 3235-3250
47. Patil, M. L. and Sasai, H. Chem. Rec. 2008, 8, 98-108
48. Winkel, A., Reddy, P. V. G., and Wilhelm, R. Synthesis 2008, 999-1016
49. Ding, J. and Armstrong, D. W. Chirality 2005, 17, 281-292
50. Baudequin, C., Bregeon, D., Levillain, J., Guillen, F., Plaquevent, J. C., and Gaumont, A. C. Tetrahedron: Asymmetry 2005, 16, 3921-3945
51. Rizvi, S. A. A. and Shamsi, S. A. Anal. Chem. 2006, 78, 7061-7069
52. Fukumoto, K., Yoshizawa, M., and Ohno, H. J. Am. Chem. Soc. 2005, 127, 2398-2399
53. Ohno, H. and Fukumoto, K. Acc. Chem. Res. 2007, 40, 1122-1129
54. Chen, X. W., Li, X. H., Hu, A. X., and Wang, F. R. Tetrahedron: Asymmetry 2008, 19, 1-14
55. Mandal, P. K., Sarkar, M., and Samanta, A. J. Phys. Chem. A 2004, 108, 9048-9053
56. Samanta, A. J. Phys. Chem. B 2006, 110, 13704-13716
57. Boydston, A. J., Pecinovsky, C. S., Chao, S. T., and Bielawski, C. W. J. Am. Chem. Soc. 2007, 129, 14550-14551
58. Boydston, A. J., Vu, P. D., Dykhno, O. L., Chang, V., Wyatt, A. R., Stockett, A. S., Ritschdbrff, E. T., Shear, J. B., and Bielawski, C. W. J. Am. Chem. Soc. 2008, 130, 3143-3156
59. Williams, A. T. R., Winfield, S. A., and Miller, J. N. Analyst 1983, 108, 1067-1071
60. Jodry, J. J. and Mikami, K. Tetrahedron Lett. 2004, 45, 4429-4431
61. Baranyai, K. J., Deacon, G. B., MacFarlane, D. R., Pringle, J. M., and Scott, J. L. Aust. J. Chem. 2004, 57, 145-147
62. Kosmulski, M., Gustafsson, J., and Rosenholm, J. B. Thermochim. Acta 2004, 412, 47-53
63. Chen, R. F. J. Res. Natl. Bur. Stand. Sect. C-Eng. Instrum. 1972, A 76, 593-606
64. Fasman, G. D. Handbook of Biochemistry and Molecular Biology, Proteins, I, 3rd ed.; CRC Press: Boca Raton, Fl, 1976.
65. Leroy, E., Lami, H., and Laustria, G. Photochem. Photobiol. 1971, 13, 411-421
66. Longwort, J. W. Biopolymers 1966, 4, 1131-1148
67. James, T. D., Sandanayake, K., and Shinkai, S. Nature 1995, 374, 345-347
68. Liang, X. F., James, T. D., and Zhao, J. Z. Tetrahedron 2008, 64, 1309-1315
69. James, T. D., Sandanayake, K., and Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910-1922
70. Wang, W., Gao, X. M., and Wang, B. H. Curr. Org. Chem. 2002, 6, 1285-1317
71. Leung, D., Folmer-Andersen, J. F., Lynch, V. M., and Anslyn, E. V. J. Am. Chem. Soc. 2008, 130, 12318-12327
72. Leung, D. and Anslyn, E. V. J. Am. Chem. Soc. 2008, 130, 12328-12333